


Castiel's Newest Pledge

by thewinchesterlifestyle



Category: Supernatural
Genre: Age Difference, Bottom Dean, Coming Untouched, Dean's First Time With a Man, Dean/OMCs - Freeform, Dirty Talk, Double Penetration, Double Penetration in One Hole, Exhibitionism, Face-Fucking, Fingering, First Time Bottoming, Fraternities & Sororities, Fraternity President Castiel, Gangbang, Heavy Drinking, Jock Dean, M/M, Manipulative Castiel, Marking, Multi, Name Calling, Orgasm Delay/Denial, Paddling, Pledge Dean, Possessive Castiel, Public Sex, Rough Sex, Sexual Coercion, Sharing, Slut Dean, Spanking, Spitroasting, Student Castiel, Student Dean, Student Jimmy, Teasing, Top Castiel, Underage Drinking, Voyeurism, also...so much sex...so much, at times it is, blackout drinking, dubcon, for various reasons, jockstrap, kind of fuck buddies (they don't have an actual relationship), very dubcon
Language: English
Status: Completed
Published: 2016-08-16
Updated: 2016-08-16
Packaged: 2018-08-09 02:04:28
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 9,620
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7782625
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: <blockquote class="userstuff">
              <p>Castiel is the president of one of the most prominent fraternities on campus and Dean is one of the new pledges. He takes matters into his own hands by claiming the pledge right off the bat and seeing just how far Dean will let him go.</p>
            </blockquote>





	Castiel's Newest Pledge

**Author's Note:**

> Written for a series of prompts in the same verse.
> 
> (nsfw gif below)

Castiel had been thinking about it the second he’d laid eyes on the beautiful green eyed pledge. Those full lips and that tight body had more than a few thoughts racing through his mind. There wasn’t a question for who was going to be handling Dean Winchester. Castiel was very interested in finding out exactly how far Dean would let him go.

They didn’t call it  _hazing_  anymore but that was clearly what it was and the defiant look on the face of pledge in front of him had Castiel spinning the paddle in his hand. He arched a brow and watched Dean glance around the room, Castiel’s bedroom, before slowly pulling down his pants.

“Over my lap.” the words were soft and he could see Dean shudder as they washed over him. “Now, Pledge. Make sure to keep count.”

Dean twitched and approached him before lying over the fraternity president’s lap. His breathing was rougher and Castiel grinned as he reached to yank Dean’s underwear out of the way and earning himself an indignant sound. But Dean didn’t protest and laid there as Castiel brought the paddle down on his pert ass once. Dean jerked and gritted his teeth as Castiel started to deliver each blow with the paddle.

The numbers stumbled out of Dean’s mouth as Castiel continued to smack his ass with the paddle and red slowly started to blossom on pale skin.

Dean’s ass felt like it was on fire and he managed to keep from crying out at the pain. But just as quickly as it started the president of the fraternity stopped. Castiel’s hand was stroking over the warm flesh and Dean whimpered slightly at the pain but he would take everything that Castiel gave him. Dean wasn’t giving up and he was going to be accepted into this stupid fraternity because his whole fucking family had been in it.

Green eyes clenched shut against the burn and little sparks of pain when Castiel leaned to pull something out of his bedside table. Dean felt him pause and didn’t know that Castiel had decided to see how far the beautiful little pledge was going to let him go. The opening of a bottle reached Dean’s ears but he didn’t think anything of it until his cheeks were being parted.

It had his whole body stiffening but he didn’t say anything. Dean laid there as a slick finger circled his hole and slowly started to push inside. He clenched down on instinct and felt the burn of an unexpected stretch as Castiel fucked one of his fingers inside with short little motions. It wiggled and twisted and crooked inside him as he released a sound at the feeling. Castiel kept a good grip on him as he moved and Dean felt another finger pushing inside.

They scissored and stretched him as he whined lowly at the feeling. “Something the matter, Pledge?” Castiel’s voice had Dean shakily jerking his head. “Do you want me to stop?”

“No, Sir.” the words were rough and Dean forced himself to lay there limply as Castiel fucked him with his fingers.

In and out.

In and out.

In and out.

Then suddenly Castiel was turning them inside him and brushing against something that had a moan dropping out of Dean’s mouth. The fingers stroked that spot until Dean was trying to rock into Castiel’s leg for relief. “You sound like a whore, Pledge. Is that what you are? A little whore?” Castiel smirked and kept stroking as Dean stiffened at his words. At that feeling Castiel stopped and resumed moving his fingers until he added another.

Dean whimpered at the loss of building pleasure but the burn of three fingers had him squirming again. “Oh.” it whooshed out and Dean’s fingers clenched as he tried to rock forward for some kind of friction but Castiel held him in place.

“No.” he pulled his fingers out and stared down at the back of Dean’s head. “Strip down and entice me into fucking you.” Castiel smacked his hand down on Dean’s red ass and had Dean yelping, “Make me want you in my fraternity. Show me how badly you want it.”

A sound escaped and Dean shifted before getting up to stand on his unsteady legs. His fingers tugged at the hem of his shirt and he stared at the handsome guy in front of him. Castiel’s face was blank and Dean knew he could walk away. He pulled off the shirt and moved to remove the rest of his clothing that was threatening to hobble him.

It was just sex.

He stood there completely naked before Castiel and glanced over at the bed before looking back uncertainly. He’d never been fucked by a guy and he had no idea what kind of pose would  _entice_  Castiel.

Dean knew about guys getting bent over and adopted that position. He laid himself out over the edge of the bed and spread his legs as his ass was presented to Castiel who had moved off the bed.

“Bent over? Does the little whore want me to fuck him while he’s bent over my bed?” Castiel stroked a hand over Dean’s burning flesh and smirked at the sound that escaped. His thumb moved down and over the open little hole before pushing in slightly to another soft sound.

He stripped himself down, rolled on a condom and slicked himself up. Castiel paused for a moment, stroked at Dean’s hip, before he leaned forward to press the pledge into the bed. His breath brushed against Dean’s ear and he grinned at the shudder. They stayed like that and he could feel Dean pushing his ass back towards where Castiel cock rested against him.

“Do you want me to fuck you?” he asked as he rolled his hips forward to brush them together. “Do you want to be split open on my cock and moaning for more? I’ll ruin you for everyone else.” his tongue brushed against the shell of Dean’s ear.

“Yes, Sir.” it was breathless and Dean moaned again when his cock brushed the bed as Castiel simply rocked up into him.

Castiel leaned back and slowly guided himself inside Dean’s tight little hole. It clenched around him and he gritted his teeth as he kept moving forward in short little thrusts until he’d buried himself inside the whining pledge under him.

The prep job he’d given Dean made the pledge’s ass one of the tightest he’d fucked and had his eyes rolling in pleasure at the clench of it around him.

Dean’s fingers were fisting the sheets and he’d shoved his face down to cover up the sounds escaping. It burned and stretched and he felt like he was being split open. Castiel draping over him and stroking his sides had him relaxing until he rolled his hips back before pushing in once more.

The pace started off slow and Castiel listened carefully to the sounds the younger guy under him was making until he heard a moan. It was low and soft as Dean clenched around him. Changing his angle had more of those sounds escaping and Castiel grinned when Dean tried pushing himself back into the thrusts.

Dean was hot and tight around him, hole fluttering with each thrust, as Castiel fucked forward at an increasingly quick and rough pace. The soft moans had gotten louder and Dean was actively trying to meet Castiel’s pace. “You’re so obedient.” Castiel’s voice was rough and he stopped holding back the sounds at the feeling of pleasure he was getting.

Underclassmen always seemed to be the biggest sluts and pledges were very quick to do everything in their power to get offered a spot in his fraternity.

The pledge under him felt so amazing around him, “Oh.” it punched out and Dean’s mouth dropped open as his cock brushed against the bed with each rough thrust.

“So  _tight_.” Castiel gripped at Dean’s hips and kept snapping his hips forward but he was already thinking about fucking the pledge again. He was going to drag this out through the whole thing until they decided on their new members. Having a warm and tight body to get lost in was too good to pass up especially one like Dean.

It would be a waste not to take advantage of such an opportunity.

He kept pounding inside Dean until his orgasm had him moaning, mouth dropped open, as he lost himself in the pleasure. Dean laid under him a whining mess as he pulled out and pulled the condom off. “Was that your first time with a guy?” he asked curiously even as he enjoyed the buzz rushing through him.

Dean nodded and Castiel watched how Dean reached for his own cock and moaned as he jerked himself to his own orgasm. With a pleased grin Castiel looked around and his eyes settled on the permanent marker on his desk. Slowly he crossed the room, grabbed it, before coming back and writing right above Dean’s ass in bold letters.

_Property of Castiel Novak_

* * *

 

Castiel narrowed his eyes as he watched a few of the cheerleaders leaning against Dean after the game. They were smiling up at him and leaning far too close to him. But they were not Dean’s only admirers. It was more than evident that several of the other guys on Dean’s team and from the stands were interested.

He could see the way they watched Dean’s ass and how they interacted with  _his_  pretty freshman. A few times he’d heard comments from others about how they’d like to bend Dean Winchester over and fuck him until he couldn’t walk right. He had to grit his teeth and stop himself from reacting in the violent manner in which he wanted to act.

But it was after one of those games that Castiel created a new rule.

“You’re only allowed to wear your jockstrap when we’re alone.” Castiel watched Dean’s cheeks flush as he stared up at the fraternity president who arched a brow when Dean hesitated but eventually complied.

After that day Castiel made Dean keep several pairs in his room so that the instant he came into Castiel’s space he was stripping down and putting one on.

The straps framed Dean’s tight ass perfectly and if Dean wanted release when Castiel was fucking him he had to come untouched. It was one of Castiel’s favorite things about the jockstraps. Dean had to work for a release and Castiel enjoyed how Dean had to rely on his cock alone to get off when they were fucking.

Sometimes he let Dean ride a large dildo until his legs were shaking and he was begging for the release just out of his reach.

Dean swallowed as he stepped into Castiel’s room and noticed the fraternity president wasn’t there yet but he dutifully stripped off his clothing and went to Castiel’s dresser before he pulled out one of his jockstraps. It always left him feeling exposed and vulnerable to wear nothing but that one article of clothing but at the same time sent a thrill through him.

His eyes flicked around the room and with a sigh he wandered over to Castiel’s bed before falling on top of the sheets in a sprawl. He dragged one of the pillows close and shoved his face in it before relaxing into a light doze. It had been a long day and he could nap until Castiel showed up.

That was how Castiel found Dean. The pretty pledge stretched out on his bed, naked save for the jockstrap, with that pretty ass on display for him.

A slow grin stole over his features as he moved through his room to find his camera and then he moved back to the bed to take a few pictures. It seemed a waste to have such a pretty image not captured and he resolved to change that. He’d take some pictures of Dean’s ass after a good spanking and some of it after a good fucking. All of the pictures of Dean’s plump ass with the perfect framing of his jockstrap.

Maybe he’d take a picture after he used Dean’s mouth or one after he came all over that pretty face and body.

He carefully set the camera down and without warning brought his hand down on Dean’s ass. A yelp escaped and Dean’s whole body jerked as he tensed up at the sharp sting coming awake in an instant.

“Fuck!” Dean started to turn around but Castiel pinned him in place. “Castiel?”

“You should always be spread out on my bed waiting to be fucked.” Castiel breathed out against Dean’s ear and the pledge could feel the fraternity president’s cock pressed against his very bare ass. “You always look so inviting with just that on.” his tongue moved along the shell of Dean’s ear and he shuddered at the feeling as Castiel shifted his hips up against Dean’s ass. “And it is  _Sir_. Do you understand,  _Pledge_?”

“Yes, Sir.” Dean pushed back into him and moaned softly as he was pressed harder into the mattress while strong hands kept his wrists pinned to the sheets.

“You’re  _mine._ Do you understand that?” the possessive words had Dean nodding his head rapidly as Castiel pulled back to reach for the lube.

Castiel was quicker in his prep as he worked one finger inside Dean’s ass, stretching, until he could push another. He pumped them in and out quickly as Dean shoved his face into the pillow in front of him. Dean could feel his cock straining against the jockstrap and he wanted nothing more than to grip himself. He wanted to fuck his own fist for release but that wasn’t allowed.

It was  _never_  allowed.

Three fingers worked inside him and brushed against Dean’s prostate to earn a high needy sound. Dean clenched around the fingers and shoved himself back into them with another moan as he tried fucking himself on them. He rocked back until Castiel swatted his ass. “No. Now be a good little whore and stop being so greedy. You’ll get what you get.”

Dean’s cheeks flushed while his cock twitched at the words. He swallowed roughly as Castiel continued and he had to force himself not to rock back into the older guy for some kind of release.

Castiel’s fingers retreated and Dean could hear clothing hitting the floor before the bed shifted with Castiel’s weight returning. A couple pillows were shoved under Dean’s hips to raise them up before Castiel shifted himself close. The blunt head of Castiel’s cock pressed against Dean’s hole before Castiel fucked forward quickly to bury himself inside in one quick, hard snap of his hips.

Dean’s mouth dropped open at the sudden stretch and he whined as one of Castiel’s hands pressed against the side of his head to hold his face against the mattress. His ass burned at the quick prep job and the rough pace Castiel immediately started up.

It was rough, as most of them were, with hips snapping forward rapidly and Castiel’s moans filling the air along with rough words to follow anytime Dean made a particularly needy sound.

"Such a greedy little whore, aren’t you?” Castiel snarled the words as he continued to slam forward but his hand never strayed from where it held Dean. “Bet you’d bend over and let the whole frat fuck you if they wanted.” his other hand, the one not on Dean’s head, tightened where it rested. “You’d just lay there and let them all use you, fill you up, like a dirty little whore begging for more.”

Dean moaned lowly and shoved his hips back into the thrusts to take Castiel as deep as possible. Each time that thick cock brushed his prostate Dean moaned brokenly and shoved his hips back into the thrusts in the hopes that one of them would set him off.

He had  _never_  expected to love getting fucked so much or to love how good it felt to be achingly full.

“So fucking greedy.” Castiel’s thrusts were brutal and Dean clenched around him as another one managed to hit his prostate. Pleasure was burning in his body and he knotted his hands in the sheets as Castiel just kept using him.

And it was the way that Castiel did so, the objectification and dirty talk, that had arousal flaring through Dean’s whole body every single time. He’d never imagined this kind of relationship, something just a little beyond fucking, but Dean kept coming back for more. He kept bending over or lying down or opening his mouth or following instructions as Castiel found more creative ways to fuck him or mark him up.

He loved being used and fucked and spanked and ordered around.

Fingers shifted and tugged at Dean’s hair, sharply, as Dean listened to more filthy words falling from Castiel’s lips. Castiel’s voice was rougher and his thrusts were not as precise but Dean was too lost in sensation.

“My pretty little  _slut_.” Castiel was getting close to the edge and Dean could feel it in the other guy’s body. “You’re  _mine_  and all those others…those  _fans_  of yours can only imagine doing a fraction of this.” Dean would have marveled at how Castiel managed such a sentence but his orgasm was building rapidly as he fell over the edge without being touched. “That’s it. Come on my cock fucking that tight hole of yours.”

Dean went limp against the sheets as Castiel kept thrusting until he buried himself deep and came with a cry of satisfaction. His body draped over Dean’s as he enjoyed the sensation of his orgasm before pulling back and slipping free.

The bed moved as he climbed off and Dean lay there recovering. His cheeks were flushed and he wanted to slip over into another doze but he felt himself being shifted. Fingers touched him and he felt his cheeks being parted before the sound of a camera caught his fuzzy attention.

It went off a few more times before those fingers disappeared and then another digital shutter sound caught his attention. “Such a pretty well fucked hole.” Castiel’s voice held satisfaction as he moved across the room and Dean’s eyes widened as he finally realized what Castiel had just done. “Think I’m going to fill up a whole folder with you. Maybe a few videos”

Castiel moved back across the room and Dean blinked at him as he opened his mouth to protest the photographic evidence of what Castiel did to him. “Ca-” he was cut off.

"Shhhh.” Castiel was grinning as he pressed their lips together while knotting his fingers in Dean’s hair. “You were made to be photographed. Especially after being thoroughly used.”

* * *

 

Castiel had noticed some of the others in his fraternity staring at Dean. He had noticed the glances and heard the whispers. But Dean wasn’t for them and Castiel was tired of them thinking they had a shot at the pretty green eyed freshman. So he waited in his room for Dean to come upstairs, watched Dean stripping down to nothing but a jockstrap and stood up to move towards the door to make sure it stayed open enough that everyone in the fraternity could hear.

He was going to make a point.

“Across my lap.” his voice was soft and calm as Dean blinked at him before he was slowly walking towards Castiel. He lay over Castiel’s lap, felt the steadying hand on the small of his back, as he tensed slightly in preparation.

He didn’t have to wait long.

The paddle came down on his bare ass and had a startled cry escaped before he started counting. Castiel always wanted him to count his swats. He whimpered and felt his face flushing hot as Castiel kept spanking his ass until it was impossible for Dean to get a number out.

He sobbed at the burning pain in his ass as tears trailed down his flushed cheeks and dripped onto Castiel’s floor.

“You’re getting better at lasting longer before crying.” Castiel praised as he stroked a hand over the hot flesh of Dean’s ass and enjoyed the view. “If only I could just keep you in my bedroom like this all the time. You’re so beautiful in nothing but a jockstrap. The perfect little bottom. Made to take cock in your plump ass.”

Dean looked like he was about to protest when Castiel had Dean straddling his lap but he didn’t give Dean a chance as he jerked him in for a possessive kiss. Long fingers knotted in Dean’s short hair and jerked his head back for Castiel to bite at his neck. A helpless moan escaped and Dean’s fingers tugged on Castiel’s shirt as Castiel easily dominated him completely.

His moans got louder and louder as Castiel teased him before he found himself spread out on the bed while Castiel grabbed a bottle of lube. Slick fingers found Dean’s hole, pressing against it and one pressed inside. It pumped slightly inside him as Castiel waited for Dean to adjust before he added a second finger. The two digits twisted and crooked to pull more of those moans out.

“Please Sir  _please_!” the begging had Castiel fucking his fingers into Dean’s tight ass quickly before moving them to press against his prostate. He teased the spot until Dean was near sobbing for relief and inserted a third finger.

It was a few more thrusts of them until he was pulling them out and flipping Dean over so he was pressed down on his belly. Cold lube was squirted directly into Dean’s loose hole and had him yelping at the sudden feeling. “Want my cock, don’t you?” when Dean didn’t respond Castiel delivered a hard smack to his ass.

"Yes, Sir! I want your cock. Please fuck me, Sir.” with his ass presented, legs off the bed, he spread them wider. The pose gave Castiel a perfect view of Dean’s still red ass as the copious amounts of lube he’d squirted inside Dean slowly started to leak back out. He reached for his camera and took a few pictures of the sight, the jockstraps framing Dean added to the beautiful image, 

“I think I need motivation today.” Castiel smirked when he heard someone in the hallway. “Don’t hold back. Moan like the whore you are.”

He lined himself up and thrust forward into Dean, “Fuck.” Dean clenched around him and shifted his legs as best he could at the position over the edge of Castiel’s bed.

“That’s right. Such a little slut for my cock.” he gripped Dean’s hips and snapped his hips forward quickly as he pumped through the mess of lube inside Dean’s hot little hole. “Come on,  _Dean_.” he purred the name and watched how fingers tightened in the sheets.

"Harder! Please Sir harder.” with a change of angle Castiel’s thrusts had him hitting Dean’s prostate and sending higher moans, louder words begging for more, bouncing through the room.

Dean was practically wailing as he begged for relief.

There was no way the other brothers and pledges couldn’t hear him begging Castiel to give it to him harder. “Such a good little bottom. A perfect  _whore_.” he grinned as the words came out rough. “You love coming on just my cock. Love feeling it fucking through you, splitting you wide and shoving deep inside you. My pretty little whore.”

Castiel grabbed the camera resting next to Dean on the bed and took a few pictures of his cock thrusting inside Dean’s ass before depositing the camera on the bed.

Dean shoved back into it and his hole squeezed Castiel’s cock as it kept working inside him. “Oh oh that’s—” Dean could feel the warmth of pleasure building in his body and a whine escaped when a hand pressed down on his lower back. “ Sir please!” he choked, “Sir, so good…ohhhh please please please! Yessss oh yes ohhhhh  _there_!”

Several more brutal thrusts, skin slapping against skin, had Dean coming with a shout as he ended up limp over the bed as Castiel fucked into him. Each thrust moved him against the bed until the fraternity president buried himself deep as he came with a satisfied moan. “I could fuck you all day.” it was something he said often and Dean moaned softly as that thick cock slipped from him.

There were a few more pictures, Castiel always adding to his collection, before a plug was pushed inside Dean’s puffy little hole. “ _Cas_.” it was breathed out and Castiel rolled Dean back over before dragging him up for a possessive kiss.

* * *

 

A moan slipped from Dean’s lips as fingers rubbed against his tight hole, teasing and pressing, as a hard cock rocked up against his own.

“Been thinking about this for awhile.” The rough voice breathed against his neck as Dean whimpered lowly. Arousal curled inside him, warming and twisting, as a finger nudged against his hole. “Been thinking about your ass spread open on my dick.”

His breathing stuttered as his mouth dropped open.

A few seconds passed before he found himself yanked forward and towards the bed. He let himself get shoved down onto the sheets, yanked into position, before the sound of a drawer opening had him glancing over.

“I’m going to fuck that ass of yours until the only thing you can do is moan for more.” The words had liquid heat building inside him as Dean’s cheeks flushed with arousal.

It was all Castiel’s fault, really, that he practically _craved_ the feeling of being manhandled and fucked. For Dean it was both a blessing and a curse because the time Dean had free between classes was the time Castiel was in class.

Fortunately Dean had discovered he didn’t lack interested partners when it came to fucking. He had stopped keeping track of how many guys he'd had fuck him since Castiel had first spanked and fucked his ass.

Lube wet fingers rubbed against his hole before one was worked inside. The guy, Mark, was rough and quick with the prep job. Thick fingers worked Dean open, rubbing against his insides and brushing his prostate until Dean was near sobbing with need, as Dean tried to reach under to touch himself.

“No touching.” His hand was pulled away and pressed into the mattress. “I want you coming when you’re wrapped around my dick.”

Three fingers twisted inside him and slipped out before Dean heard the wet slide of a palm moving over a cock.

Mark’s breathing hitched as he stroked himself and Dean’s breathing quickened as the mattress shifted when Mark moved closer. His hips were raised up, knees bent slightly and pressed to the mattress, as Mark shoved himself inside with a greedy moan.

“Fuck.” He breathed out roughly as he braced hands on either side of Dean, “Knew you’d feel good.”

The pace started off relatively slowly as Mark lifted himself up, pulling out and slamming back inside, as Dean shuddered at the sensation of being fucked. His cheeks flushed and his mouth dropped open as breathless moans started to escape.

“Ohhhh.” His cock ached and Dean desperately wanted to touch himself, he wanted to reach down and jerk himself in time with Mark’s thrusts, but he stopped as a hand moved over to hold his wrists down into the mattress. “Please, Mark, please!”

The pace was maddening as more thrusts had Mark hitting his prostate than missing. His moans got louder and louder as Mark started to pound into him, the hard slap of skin against skin filling the room, as Dean’s fingers yanked at the sheets.

“You’ve got an ass made for fucking.” The words were moaned out as Mark’s hips smacked against Dean’s ass. “Fuck.”

Dean started to shove himself back as his hole clenched and the pleasure inside him built. He could feel his orgasm right there on the edge but Mark wasn’t fucking him in a way that was going to send him over the edge and it had Dean practically sobbing with a desperate need to come.

“Love this, don’t you?” Mark’s teeth scraped against Dean’s shoulder, “Love taking dick. I can tell.”

“Yes!” Dean agreed hoping Mark would touch him or let Dean touch his aching cock. “Please please I need—”

Soon Mark was slamming inside him, the pace off and rough, as Dean moaned brokenly. That was when Mark reached under and it only took two strokes before Dean was wailing his release. His entire body tensed as his orgasm rushed through him before he was sprawled out limp on the sheets with Mark pounding into him.

Each thrust had him shuddering until Mark slammed inside and came with a pleased groan.

“You’re a hell of a fuck, Dean.”

The only thing Dean could do was moan lowly as Mark’s softening cock slipped from his aching hole and his ass clenched down on nothing.

After a few minutes of catching his breath Dean shifted and managed to get off the bed on shaky legs. He could feel Mark’s come steadily leaking back out of his puffy hole and a glance over revealed a very smug looking Mark watching him.

“Any time you want a good fuck feel free. I’m more than interested in seeing how flexible you are.”

The words had Dean swallowing at a memory of another guy, from his English class, who had bent him in half and fucked him hard enough that Dean had winced each time he’d shifted in his seat during the rest of his classes that day.

“Sure.”

After quick clean up and getting dressed Dean slipped out of Mark’s dorm, ignoring the appraising looks he received from several guys in the hall, before heading towards his last class.

Hours later Dean headed towards the frat house, a new number in his phone and a very interesting proposition from one of his teammates that he was more than interested in. He had several hours to kill between classes on Friday and Dean wouldn’t mind spending them with Jacob. Dean was so interested that he'd already agreed to it and made plans for learning how good of a fuck Jacob actually was.

He slipped inside the house, nodded towards the brothers he saw, before moving further inside.

Dean glanced at the stairs and then back at his fraternity brothers before heading towards Castiel’s room. He’d grown attached to the fraternity president and idly he wondered sometimes if he wasn’t a little bit masochistic because he had come to enjoy Castiel spanking his ass until it burned. Dean had also found he preferred coming untouched and the way Castiel would press kisses against him in a silent reward that had warmth curling in his body for a completely different reason.

It was nothing on how much he loved getting fucked hard and rough until he felt it hours later, sometimes days later.

He reached out and turned the knob before walking into the room. His bag hit the ground and he automatically moved to the dresser to grab a jockstrap before changing. It was kind of freeing wearing nothing but the jockstrap as he sprawled out on Castiel’s bed to play a game on his cell phone.

The sound of it filled the room before he reached back to grab a pillow to shove it under himself. It smelled like Castiel and he sighed out as his fingers moved against the touchscreen with clear familiarity.

That was how Castiel found him after his class. Perfect ass framed by black straps and laid out on his bed like a good boy. He didn’t even pause in taking a picture, Dean should be photographed, and then he dropped his bag next to Dean’s so he could cross the room.

“That room of yours is basically only for storage.” he sounded far too pleased and Dean glanced up at him with an arched brow. “You should just stay in my bed all the time. Waiting for me. Waiting for me to fuck that gorgeous ass of yours.” he pressed a kiss against Dean’s shoulder blade before moving down Dean’s body to bite lightly on Dean’s ass. It earned him a rough sound that only encouraged him. “You really have become such a slut for it, haven’t you?”

“I have kind of gotten used to being fucked on a daily basis.” Dean paused his game and glanced back at him. “It’s like Pavolv’s dogs.”

“Are you calling yourself a dog?”

“No. But you’ve conditioned me regardless. Now I get hard every time I put on a jockstrap just thinking about what you do to me in them. It makes practice and games awkward as fuck.”

Castiel’s fingers tightened against him, “You make sure you remember you're  _mine_. Those other people can back the fuck off.” the possessive tone had Dean twisting around so he could look up at Castiel as the older guy moved to hover over him.

He wasn’t going to mention that he had, actually, given several of the guys on the team a test drive between classes and once in the locker room. And that wasn't even going into the number of guys outside of his team that he'd offered up his ass and mouth for use.

Dean really,  _really_  enjoyed getting fucked.

Castiel’s eyes were dark and Dean shuddered at the look on Castiel’s face.

“Pretty sure most of the campus has figured that out. You’re not very subtle.” It was the best thing to say because admitting he’d been fucked by others wasn’t going to help him. At all.

He had wasted so much time  _not_  getting fucked and it was hard to resist temptation when there were so many guys always interested in fucking him. The only thing he'd asked, after he'd been fucked, was that they not spread it around and he'd be  _more_ than interested in multiple repeat performances.

It had worked beautifully so far and Dean had more than enough interested guys both on campus and off he could call if he needed an itch scratched at any given time. Being a good fuck paid, after all.

Dean tilted his head back when Castiel moved down for his neck, biting lightly as he worried a mark into the skin, before he settled his body against Dean’s.

The fraternity president loved pressing Dean’s body down into the mattress, loved feeling those muscles under him, as Dean had to rely completely on him and his touches to get off.

The power of it gave him a rush that had his cock pressing hard against his pants and a low growl escaping when Dean’s hands gripped at him to pull him even closer.

“Come on, Cas. Quit teasing.” Dean pushed his ass up against Castiel’s hard on. “I know what you want to do.”

That was all Castiel needed as he climbed off, stripped rapidly and grabbed the bottle of lube before getting back on the bed. He was quick and efficient as he stretched Dean open, teasing a few times, as Dean moaned under him.

Dean was always very responsive and Castiel mentally patted himself on the back for taking over Dean when the freshman had been a pledge. “Always so hungry for me.’ Castiel grinned as he pumped his fingers inside Dean’s clenching hole before withdrawing.

" _Please_.” Dean could feel Castiel moving him and lifted his hips so a pillow should be shoved under there. It lifted him just enough as Castiel climbed on top of him before his cock was pressing inside.

It filled Dean up and stretched him open in all the right ways as he moaned at the feeling. Castiel never prepped him enough so there was always that delicious burn of his ass stretching to accommodate Castiel’s large cock.

The bed shifted as Castiel began snapping his hips forward, hands splayed out against Dean’s skin, as moans filled the room. Dean was always so tight and hot around Castiel, squeezing just right, as Castiel moved quickly inside him.

There were times that Castiel would draw it out, make Dean cry and beg for it harder, but today it seemed that Castiel was in it to get off instead of tease. He wanted a fuck and nothing else.

“I love fucking you into the mattress. You have such a greedy little hole. Always taking my cock so well.” each sentence was rough with arousal and Dean moaned when that thick cock hit his prostate. Every strike sent a warm jolt of pleasure through him until he thought he might shake apart.

“Oh please harder Sir harder there ohhhhh there yes!” Dean shoved himself back as best he could into each thrust, feeling Castiel going balls deep with every single stroke, until he came on the feeling of Castiel fucking him while Castiel moaned with appreciation.

It had him tightening even more around Castiel, mouth falling open, as he enjoyed the rush of pleasure filling him up. He was limp under Castiel, shaking and whining softly, as Castiel kept fucking forward until he finished with a pleased sound.

* * *

 

Dean was still sleeping off the enthusiastic sex he’d enjoyed with Castiel, ass stretched around a plug and semi-hard cock still resting in his jockstrap, when the knock came against the door. “Come on Winchester! There is a party going on downstairs.” he twitched on the bed and got to his feet before looking around for pants.

Once he was presentable Dean stumbled down the stairs and found a glass pressed into his hands. “Hiding away upstairs.” one of the fraternity brothers shook his head and Dean offered a slight smile. A glance around let him know that Castiel was nowhere in sight but he didn’t let that stop him from enjoying the party.

Hours and lots of drinks later found him tugged down onto one of the fraternity brother’s laps as the guy sucked a mark into his skin.

“The frat slut.” a voice spoke from behind him and Dean’s brow furrowed as he tried to focus on the words but the alcohol kept him fuzzy. Instead he leaned into the warm touches and the grasping fingers as his shirt was thrown to the side. “That’s it. Let’s get a look at that body of his.”

Dean felt himself tugged up and he swayed as hands steadied him while his pants were tugged down to reveal the jockstrap he’d left on. “Look at that. No wonder Novak enjoys pounding his ass if he wears things like that under his pants.”

“Did you hear him last week? He  _loves_  getting fucked.”

A soft moan escaped Dean when hands started moving back over him and fingers found the plug to tug it out. “Come on pretty boy. I want you to ride my dick, show me what Novak enjoys so often. Show me what has him coming back for more of your tight ass.”

Dean was guided down to straddle the original fraternity brother’s lap and he felt a cock at his slightly stretched open hole before it was pressing inside him. He moaned at the burn and shoved himself back into it as a mouth attacked his collar bone with enthusiasm.

“Fuck. Look at him.” a voice came from behind him and Dean wasn’t paying attention as hands fell to his hips before they were thrusting up into him. The only thing he was focusing on was the warm and fuzzy feeling of being too drunk and a cock moving inside him.

He  _loved_  that feeling.

“Takes it like a pro.” another laughed as they watched Dean moaning as he rode the cock buried inside him. “I’m next since this was my idea to see what we’re clearly missing.”

“He won’t mind. Winchester is a complete  _whore_.”

After the first guy came inside Dean’s clenching hole the others who had been interested made sure to take their turn. They guided Dean over the couch, braced him against a table and one of them had him on the floor until Dean was a whining mess with rug burns on his naked skin.

The five guys who had been interested and their friends spent the majority of their time in the main room with Dean, taking turns with him, as the rest of the fraternity remained otherwise engaged in drinking games, girls and alcohol.

At one point they had managed to get two cocks into Dean’s ass while Dean choked on a third, body limp and cheeks flushed, as they held him in place and used him.

Dean woke up, fuzzy and dazed, to the feeling of a thick cock pumping in and out of his ass. He could hear loud, pleased grunts and felt fingers knotted in his hair as a whine climbed up his raw throat. He tried to focus past the lingering buzz of alcohol and the dazed feeling of being half-asleep as the guy above him continued to roughly plow his ass into the ground.

He blinked and his ass clenched on reflex when the cock fucking him brushed his prostate sending a thrill of pleasure racing through him. A low, whining kind of moan escaped and earned a rough chuckle. His face was smashed further into the ground and the pace of the guy fucking him picked up.

"Fuck. Doesn't matter if you're awake or pliant with sleep...I love fucking this ass of yours, Winchester."

Dean panted as pleasure built inside of him and the alcohol still filling him kept him warm, loose and pliant on the floor. He didn't bother moving when the cock pounding into him shoved deep and a loud groan of pleasure let him know a load had just been emptied into him again. He whimpered at the feeling of a softening cock slipping from his fucked open, sensitive hole and barely had a moment to register the feeling of empty before another cock, just as hard and thick, roughly fucked back into him.

Skin slapped against skin, grunts and groans of pleasure once more met his ears, and Dean lost the battle with unconsciousness to slip back into the darkness to the feeling of being roughly fucked on the floor of the frat house.

In the morning when he woke again it was with a pounding headache, hours of the night before missing and a very,  _very_  sore ass that had him moaning when he tried to sit up. He shifted carefully and pressed a hand to his head as he tried to get the horrible pain to stop. “ _Fuck_.” his voice was hoarse and he shifted again only to hiss.

All of his muscles were signaling a wild night that he didn’t remember and looking around Dean was nowhere near Castiel’s room. He blinked and tried to figure out what had happened the night before but it wasn’t there. He could only remember coming downstairs for the party and drinking, throwing back shot after shot, before his memories seemed to slip from his gasp.

Fuck.

He’d only had a blackout drinking experience once his senior year of high school and he’d sworn to never do that again. That next day he’d been told he’d made out with half the people there and he’d ended up having sex with a girl whose name he didn’t remember. The only saving grace from that experience had been that he’d worn a condom and she’d been on the pill.

Now he was starting to worry as he got to his feet and checked himself over to realize there was dried come on him. It was on backs of his thighs, his ass, at the corners of his mouth and on his back.

He couldn’t imagine what he looked like.

“ _Shit_.” Dean groaned and looked around for his clothes before leaving the room to stumble towards his.

Dean wasn’t expecting the front door to open or for Castiel to stop and stare at him. “Dean?” his voice was low and the freshman froze before turning blurry eyes in Castiel’s direction. “What are you doing?” his eyes narrowed as he took in Dean’s state. “What happened?”

A shaky breath escaped and Dean shifted before he spoke, “I don’t know.” it was small sounding and he flushed darkly. “I don’t remember last night.” he nervously licked his lips, twitching when he tasted dried come, and watched Castiel close the distance between them.

“Let’s go upstairs. You clearly need to wash yourself off.” there was a low sounding anger in his tone as he guided Dean towards his room and left Dean under the hot spray before going back down the stairs.

He found one of his fraternity brothers passed out on the kitchen floor and nudged him with his foot. “Matt.” he hissed out and watched brown eyes crack open before looking around to land on him. “What happened last night?”

“Party.” the word was rasped and followed by a low groan.

“I gathered that.” His tone was flat as Castiel stared down at him, “What happened  _at_  the party?”

“The usual.” brown eyes closed, “Drinking, beer pong, fuck the dealer, some girls someone invited in, more drinking…” he trailed off and furrowed his brow, “Oh…there were a few guys and their friends passing Winchester around like a party favor. Think they fucked the kid most of the party.”

“What?” Castiel’s voice was frosty and brown eyes snapped open to look up at the president of the fraternity. “What exactly happened with that?”

“They got him to come down to the party and I honestly lost track of the amount of alcohol they got into him. It loosened him up and then he was getting dragged down onto Eric’s lap. After that they were taking turns with him most of the night and then he finally passed out on the couch mid-fuck. After that they fucked him for an hour or so more before they were all finished. They didn’t hurt him if you’re worried. He was moaning pretty loudly for all of it.” Matt was more alert now and that meant he could see Castiel shaking in rage.

“They got him drunk and took advantage of him, that’s what you’re saying?” he gritted his teeth, “I want names, Matt.”

Castiel stood there and listened to the other guy rattle them off before he was going upstairs to find Dean curled up on his bed hugging a pillow. Dean was under his covers and from what Castiel could see he was completely naked.

“Dean.” he spoke and watched as the freshman muttered before shoving his face further into the pillow he was clutching. “Fucking hell.” it was growled and he scowled at the soiled clothes Dean had left in a heap. He just had to go visit his brother and then his happened.

He thought on it the whole day of what exactly he was going to do and the fraternity president decided on a public display of exactly who Dean  _belonged to_  was in order.

At their next party he made sure those who had taken advantage of Dean were there when he dragged Dean down onto his cock, when Dean rode him, as he placed his hands on those perfect hips.

“That’s it. Show them who you belong to.” he growled the words and watched as Dean’s mouth dropped open. “You look perfect on my cock. Like you were made for it.” he pulled Dean down for a possessive kiss and growled when Dean’s fingers knotted in his hair. “Show them you can come on my cock only. Show them what a whore you are for it. For  _me_.”

“Fuck.  _Sir_.” Dean fisted his other hand in Castiel’s shirt and started moving his hips quicker as he clenched around Castiel. Soft moans escaped him and his mouth worked as he felt pleasure building in him.

The instant that Castiel took control of the pace Dean threw himself into the sensations. He met Castiel’s upwards thrusts and focused on the filthy words. “That’s it. My whore. My pretty green eyed slut.” Castiel’s grip left marks in Dean’s hips. He looked down at Dean’s jockstrap and wished for the view of it framing his ass but for this he would settle on Dean’s pretty face.

Dean came three thrusts before Castiel and he ground Dean down on his cock as he emptied himself inside Dean’s ass. He could feel Dean’s hole fluttering around him and grinned as he jerked Dean down in for a kiss, tongue slipping inside, before he was staring at the guys watching them.

“Anyone else lays a fucking  _finger_  on what is mine without permission and it’ll be the biggest mistake you’ll ever make. He is mine. He isn’t for any of you or your friends.” the words were growled and Dean was blinking down at him with an expression Castiel wasn’t going to analyze.

Dean shifted until Castiel’s cock slipped from his ass and then barely managed to keep in the startled sound when he was moved around so Castiel could press a plug inside. “Sir?” he managed but found himself being tugged along after the fraternity president.

They made it up to Castiel’s room and he pressed Dean back against the door. “You’re mine, right?” it was a question and Dean stared at him.

"Yes, Sir. Of course.” Dean knew what had happened and didn’t want to think about it. He wanted to forget it and pretend it never happened but if Castiel had needed that down there he had been more than willing. If anything it might discourage those assholes from touching him. Dean might enjoy getting fucked but he wanted to be fully aware of it and it needed to be something he wanted. “Do we have to go back down there?” he asked and watched Castiel shaking his head. “Good. Let’s watch a movie and later you can tie me up. I noticed the new toys in the closet.”

* * *

 

Dean stumbled up the stairs and moved down the hallway towards Castiel’s room. He wanted to either sprawl out on Castiel’s bed and either lazily jack himself off or get fucked into the mattress. Either of those options would end with him lax and resting on top of that soft bed. His hand closed around the doorknob as he twisted and pushed it open before stepping inside.

He could see Castiel flipping through his photo album and Dean offered a slight grin. “I’m surprised you haven’t framed any of those yet.” it was slightly cheeky but Dean knew it wouldn’t piss Castiel off. His fingers went to his clothes and he started stripping them off.

What he didn’t notice was the widened blue eyes or the way the man he thought was Castiel started shifting in his seat.

Dean’s clothes fell to the ground and he stepped out of them to glance over at the fraternity president. “You going to stare at me or are you going to fuck me,  _Sir_?” he asked as he crossed the room and pressed himself against who he thought was Castiel. He was always inevitably hornier when he got alcohol in his system and he had just enough that he really wanted Castiel to fuck him so he could pass out with that sated feeling.

“I do-” Dean cut him off by pressing his hips against the other guy’s and knotted his fingers in his hair.

“ _Please_. I even wore a jockstrap for you. I know you love fucking me in them.” Dean was rapidly shifting from any thought of sleep and right into sex.

“You have the wrong-”

The door opened and shut as Dean blinked before glancing over to see Castiel. “What the-?” he turned back to the man he was pressed against and then back over to Castiel.

“Don’t stop on my account.” the man leaning against the door actually smirked. “What haven’t we shared, Jimmy?” he asked and watched Dean’s mouth drop open.

“Twins.” he sounded so surprised and it had a laugh escaping Castiel. He stared at the guy he was touching, “You’re not Cas.”

“Jimmy.” the guy spoke and his voice was slightly different from Castiel’s. It wasn’t as deep but it still had Dean reacting. It was also rough with clear arousal. “I thought  _this_   _one_  was  _yours_.” he didn’t stop himself from touching Dean’s body in front of him.

“I’d only ever share him with you. You’re the exception. You’re  _always_  the exception, Jimmy.” Castiel moved away from the door towards them. “What do you think about getting fucked by twins, Dean? You want to show my brother what a pretty little whore you are for cock?” his fingers brushed through Dean’s hair and he watched Dean lean into the touch without thought. “Or are you hoping I’ll punish you for not knowing this wasn’t me? Do you want me to spank your ass red and fuck you into the mattress? Maybe while Jimmy uses your mouth?”

“Maybe when he is more sober.” Jimmy spoke softly and watched his twin look at him. “As much as I love drunk fumbling and messy, wild sex I do enjoy knowing that flush is because of me and not alcohol.”

Castiel shrugged, “I would hope you enjoy drunk fumbling.” he smirked and glanced at Dean. “He could help you with that.” he nodded towards Jimmy’s erection and watched his twin’s eyes darken. Castiel knew how much Jimmy loved blowjobs. “Dean…do you want to blow my brother while I’m pounding away in that tight ass of yours?”

Dean nodded and allowed himself to be dragged up as he was guided towards the bed.

“Stretch yourself open for me.” he watched Dean reaching for the lube and smirked as fingers fumbled before they were working inside. “See how greedy he is for it, Jimmy? I hold you about him.” Castiel pressed a kiss against his brother and dragged him up. “I’m thinking hands and knees or you could lay down and we could do it that way.”

“I don’t care.” he shrugged and watched Dean fucking himself with his fingers. “Those pictures, Cas.” He trailed off and shuddered slightly.

“I thought you might enjoy them just as much as I do. So Mr. Photography major…were they up to your standard?”

“Pure art.” Jimmy breathed as Dean whined and spread his legs open. He wondered about the jockstrap but when Castiel ordered Dean to his knees he immediately saw the appeal. “Fuck, Cas.”

“I know. Just wait until you finally give him a shot. He’s so greedy for it and responsive.” Castiel was stripping himself and climbing up behind Dean to press him into the position he wanted. “Dean comes on my cock or nothing at all. He’s  _very_  obedient.”

He slicked himself up and pressed against Dean’s hole before glancing at his twin. “Oh.” Jimmy grinned at his twin and watched blue eyes flash wicked intent at him.

Jimmy watched as Castiel buried himself right inside Dean and he watched how the pretty freshman’s mouth dropped open at the sudden feeling of being full. “Are you going to leave that pretty mouth empty, Jimmy? My little whore hates being empty for long.”

Dean was moaning and shoving himself back into Castiel’s thrusts, greedy for his own release, as he blinked green eyes at Jimmy who was standing in front of him.

But instead of the more rough treatment that Castiel was widely known for, the touches Dean was familiar with, there were soft and careful hands stroking his cheeks. Fingers tugged lightly at Dean’s hair and moved down to touch soft lips.

Jimmy watched Dean suck his thumb into his mouth, tongue brushing against it, as he moaned around the digit. “ _Wow_.” Jimmy rewarded Dean’s actions with another soft touch to Dean’s hair and then he was pulling down with his thumb as Dean’s mouth opened. “Open for me beautiful.” he breathed out and watched Dean do exactly that.

Pretty gem colored eyes were hooded and Dean was releasing these perfect sounds as Castiel fucked him harshly from behind. Dean’s body was moving with the thrusts and the flush from earlier was darkening as Jimmy guided his now freed cock into Dean’s mouth.

He watched lips seal around him and at the feeling of wet heat surrounding him he moaned. “Fucking perfect mouth.” he placed his hand at the back of Dean’s neck to hold him in place and started up a steady rhythm as Dean got used to it. There were a few instances where he choked but Jimmy waited and watched as Dean relaxed his throat.

And then both of them were thrusting away at him at both ends. Castiel’s fingers dug into Dean’s warm skin and Jimmy holding his head in place as he thrust.

Dean came first just a few thrusts before Castiel and when the fraternity president came he buried himself deep with a pleased moan. He could feel Castiel’s pace changing as his cock emptied inside Dean.

Behind Dean Castiel watched his brother getting lost in Dean’s mouth. He could see Jimmy’s cheeks flushed, mouth open as he panted, and grinned as he stroked a hand down Dean’s flank.

“That’s my pretty whore. You’re doing so well taking care of my twin.” he breathed and watched as Jimmy finally lost himself in his orgasm as Dean swallowed down every single drop. “You’re going to let him fuck your ass next once he’s ready again.”

It was only a few seconds after Jimmy’s cock slipped from Dean’s slack mouth that Castiel heard Dean’s response that had satisfaction curling warm inside him, “Yes, Sir.”


End file.
